Windsor County Vacation Packages
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Your Windsor County Vacation
With a Windsor County vacation package, you can forget about planning hassles and instead focus on experiencing everything this exciting destination has on offer. Begin your trip to Windsor County with some time exploring Ludlow visiting popular sights like Weston Playhouse and Lake Rescue. Norwich is another top city that lures crowds from near and far. Quechee Gorge Bridge and Quechee Gorge Village are two of the leading places to see in this destination. From the instant you book your Windsor County vacation to the second you come back home, Expedia will take care of you each step of the way.
Top vacation destinations in Windsor County
Top Windsor County Vacation Deals
Price found within the past 48 hours. Click for updated prices.
Harvest Barn Inn
CA $998
per person
Oct 2 - Oct 4
found 1 hour ago
Roundtrip non-stop flight included
Toronto (YYZ) to Rutland (RUT)
9.8/10 Exceptional! (270 reviews)
We had a great stay at Harvest Barn Inn ! We enjoyed superb breakfasts created by Blessing! They are friendly and respectful hosts and the front porch view was beautiful! Parking is plentiful ! It was quiet at night and the couple was responsive by text!
Reviewed on Aug 16, 2026
Golden Stage Inn B&B
CA $1,067
per person
Oct 2 - Oct 4
found 1 hour ago
Roundtrip non-stop flight included
Toronto (YYZ) to Rutland (RUT)
10/10 Exceptional! (45 reviews)
Julie and Mike were the nicest most amazing hosts! The breakfast was fantastic, the atmosphere was perfect for rest and relaxation. Our room was clean and cool and cozy, the bathroom was nice and the bath products were great, and sold on sight. We had such a nice time! We will definitely be back!
Reviewed on Jul 6, 2026
Windsor County Hotel Deals
Align Inn Vermont
5817 Woodstock Rd Quechee VT
Fully refundableReserve now, pay when you stay
CA $149
CA $163 total
Aug 24 - Aug 25
includes taxes & fees
9.4/10 Exceptional! (1,293 reviews)
"The room smelled like smoke. The water smelled terrible coming out of the shower. Staff was nice. Budget price, but won’t catch me there again."
Reviewed on Aug 17, 2026
Woodstock Inn & Resort
Fourteen The Green Woodstock VT
CA $548
CA $663 total
Sep 7 - Sep 8
includes taxes & fees
9.4/10 Exceptional! (598 reviews)
"Amazing! Will visit again."
Reviewed on Aug 7, 2026
Holiday Inn Club Vacations Mount Ascutney Resort by IHG
485 Hotel Road Brownsville VT
Fully refundable
CA $193
CA $233 total
Aug 19 - Aug 20
includes taxes & fees
9/10 Wonderful! (865 reviews)
"Laundry room in the building, get beds."
Reviewed on Aug 16, 2026
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Frequently asked questions
How much does a Windsor County vacation package cost?
Choose from any combination of hotels, flights and car rentals, and you can be vacationing in Windsor County from just CA $998. And the more you bundle, the more cash you save. The vacation of your dreams has never been more affordable.
How do I get a cheap travel package to Windsor County?
You'll save a ton of money if you bundle your hotels, car rentals and flights into a Windsor County travel package. Sometimes cheap packages mean fewer choices. But not with Expedia. We offer over 550 airlines and 1,000,000 hotels all over the world, which means you'll always have plenty of variety to choose from. Want to save even more? Add some exciting activities to your package deal to unlock even more bargains! After all, travel is about more than simply getting to your destination.
Where should I stay in Windsor County?
Okemo Mountain Resort is one of the key things that lures people to Windsor County, so it makes perfect sense that many decide to book their hotel in Ludlow.
What are the top hotels in Windsor County?
When it comes to hotels in Ludlow, Super 8 by Wyndham White River Junction and Holiday Inn Express Hotel & Suites White River Junction, an IHG Hotel are two terrific options. If you're spending time in Plymouth, Hotel Coolidge and White River Inn and Suites will make you feel right at home.
How far in advance should I book my Windsor County vacation?
It depends on the airline, but you can usually browse through international fares on Expedia up to a year in advance. While it's advisable to book ahead of time, lucky customers will sometimes find a cheaper flight only weeks before their intended journey.
What does an Expedia Windsor County travel package include?
It comes down to what you're looking for. If you're traveling by yourself, you might decide to bundle hotels and flights. Bringing the entire family to Windsor County? A travel package that includes hotels, rental cars and flights might suit you better. Expedia gives you the freedom and flexibility to tailor your travel package.
What should I know before booking a Windsor County travel package?
You'll save big with an Expedia travel package. Combine your flights, rental cars and hotels and be rewarded with great discounts. Hotels aren't your only choice, however. Book with us and take your pick of beachside condos, chalets in the middle of mountains and even glamping tents!
Can I choose my airline with a Windsor County Expedia vacation package?
Most definitely. Expedia has more than 550 partner airlines to select from across the world. With so many choices, finding the ideal carrier to fly you to Windsor County will be a snap.
If I'm not able to travel, can I cancel my Windsor County vacation package?
We get it — unexpected stuff happens. If you've locked in a Windsor County vacation package and need to amend or cancel it, we can help. It's always worth browsing our Customer Service Portal first for information. But generally, if you've booked your package within 24 hours, you may be able to amend or cancel your itinerary free of charge. If it's been more than 24 hours, your hotel, airline or car rental company may impose a charge.
Stay near popular Windsor County attractions
Okemo Mountain Resort
9.2/10 (510 reviews)
Hit the slopes in Ludlow with a visit to Okemo Mountain Resort. Discover the mountain views in this romantic area.
Photo by Mike Gauthier
Quechee Gorge Bridge
9.2/10 (580 reviews)
Quechee Gorge Bridge is just one of the places to see in White River Junction, so why not enjoy the other things to explore during your travels? Wander the riverfront in this quaint area.
Photo by George Sykes
King Arthur Baking Company
9.4/10 (178 reviews)
You can enjoy retail therapy at King Arthur Baking Company during your stay in Norwich. While you're in the area, stroll along the riverfront.
Photo by Ed Gaffny
Quechee Gorge Village
9.0/10 (288 reviews)
You can enjoy retail therapy at Quechee Gorge Village during your trip to Quechee. Amble around the area's riverfront or seek out the ski slopes.
Photo by William E Berry Jr.
Mount Ascutney
8.8/10 (27 reviews)
Commune with nature and explore the great outdoors at Mount Ascutney during your travels in Brownsville. You can seek out the ski slopes while in the area.
Billings Farm and Museum
9.2/10 (84 reviews)
You can study the exhibits at Billings Farm and Museum, a museum with a storied past, during your trip to Woodstock. Wander the riverfront in this quaint area.
Simon Pearce Mill
9.0/10 (80 reviews)
Learn about the local history of Quechee when you spend time at Simon Pearce Mill. Amble around this family-friendly area's riverfront and enjoy its top-notch restaurants.
Upper Valley Aquatic Center
8.0/10 (43 reviews)
Enjoy a stop at Upper Valley Aquatic Center, an entertaining place to visit in White River Junction. Wander the riverfront in this quaint area.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
